1621673-53-7

Basic information

• Product Name: 4-(biphenyl-4-ylmethylsulfanylmethyl)-N-(hexane-1-sulfonyl)benzoylamide
• CAS NO: 1621673-53-7
• Molecular Weight: 481.68
• Mol File: 1621673-53-7.mol

Chemical Properties

• CAS DataBase Reference: 4-(biphenyl-4-ylmethylsulfanylmethyl)-N-(hexane-1-sulfonyl)benzoylamide(CAS DataBase Reference)
• NIST Chemistry Reference: 4-(biphenyl-4-ylmethylsulfanylmethyl)-N-(hexane-1-sulfonyl)benzoylamide(1621673-53-7)
• EPA Substance Registry System: 4-(biphenyl-4-ylmethylsulfanylmethyl)-N-(hexane-1-sulfonyl)benzoylamide(1621673-53-7)

Safety Data

• Hazardous Substances Data: 1621673-53-7(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
4-(biphenyl-4-ylmethylsulfanylmethyl)-N-(hexane-1-sulfonyl)benzoylamide is used as an anti-diabetic agent for enhancing insulin signaling and improving plasma glucose, triglyceride, and A1c levels without causing weight gain in db/db mice. Its anti-diabetic effects are suggested to occur via enhancements in insulin signaling and anti-obesity effects via leptin signaling enhancements.
Used in Neuroprotection:
In the field of neuroscience and neurology, 4-(biphenyl-4-ylmethylsulfanylmethyl)-N-(hexane-1-sulfonyl)benzoylamide is used as a neuroprotective agent for protecting neurons from cerebral ischemia. This protective effect is mediated by the restoration of tight junction proteins via activation of the Akt/FoxO1 pathway.

References

1) Morashita (2017),?Novel Non-carboxylate Benzoylsulfonamide-Based Protein Tyrosine Phosphatase 1B Inhibitor with Non-competitive Actions;?Chem.Pharm.Bull.?65?1144 2) Ito?et al.?(2018),?Therapeutic effects of the allosteric protein tyrosine phosphatase 1B inhibitor KY-226 on experimental diabetes and obesity via enhancements in insulin and leptin signaling in mice;?J.Pharmacol.Sci?137?38 3) Sun?et al.?(2018),?Neuroprotective effects of protein tyrosine phosphatase 1B on cerebral ischemia/reperfusion in mice;?Brain Res.?1694?1 4) Sun?et al.?(2019),?KY-226 Protects Blood-brain Barrier Function Through the Akt/FoxO1 Signaling Pathway on Brain Ischemia;?Neuroscience?399?89

Upstream product

• 6258-69-1 p-phenylbenzyl mercaptan 
• 3144-11-4 1-hexanesulfonamide 
• 2417-72-3 Methyl 4-(bromomethyl)benzoate 

Relevant articles and documents

Novel non-carboxylate benzoylsulfonamide-based protein tyrosine phosphatase 1B inhibitors with non-competitive actions

A novel series of benzoylsulfonamide derivatives were synthesized and biologically evaluated. Among them, 4-(biphenyl-4-ylmethylsulfanylmethyl)-N-(hexane-1-sulfonyl)benzamide (compound 18K) was identified as a protein tyrosine phosphatase 1B (PTP1B) inhibitor with potent and selective inhibitory activity against PTP1B (IC50 = 0.25 μM). Compound 18K functioned as a non-competitive inhibitor and bound to the allosteric site of PTP1B. It also showed high oral absorption in mice (the maximum drug concentration (Cmax) = 45.5 μM at 30 mg/kg), rats (Cmax = 53.6 μM at 30 mg/kg), and beagles (Cmax = 37.8 μM at 10 mg/kg), and significantly reduced plasma glucose levels at 30 mg/kg/d (per os (p.o.)) for one week with no side effects in db/db mice. In conclusion, the substituted benzoylsulfonamide was shown to be a novel scaffold of a noncompetitive and allosteric PTP1B inhibitor, and compound 18K has potential as an efficacious and safe antidiabetic drug as well as a useful tool for investigations of the physiological and pathophysiological effects of allosteric PTP1B inhibition.

Novel non-carboxylate benzoylsulfonamide-based protein tyrosine phosphatase 1b inhibitors with non-competitive actions

A novel series of benzoylsulfonamide derivatives were synthesized and biologically evaluated. Among them, 4-(biphenyl-4-ylmethylsulfanylmethyl)-N-(hexane-1-sulfonyl)benzamide (compound 18K) was identified as a protein tyrosine phosphatase 1B (PTP1B) inhibitor with potent and selective inhibitory activity against PTP1B (IC50-0.25 μM). Compound 18K functioned as a non-competitive inhibitor and bound to the allosteric site of PTP1B. It also showed high oral absorption in mice (the maximum drug concentration (Cmax)-45.5 μM at 30 mg/kg), rats (Cmax-53.6 μM at 30 mg/kg), and beagles (Cmax-37.8 μM at 10 mg/kg), and significantly reduced plasma glucose levels at 30 mg/kg/d (per os (p.o.)) for one week with no side effects in db/db mice. In conclusion, the substituted benzoylsulfonamide was shown to be a novel scaffold of a noncompetitive and allosteric PTP1B inhibitor, and compound 18K has potential as an efficacious and safe antidiabetic drug as well as a useful tool for investigations of the physiological and pathophysiological effects of allosteric PTP1B inhibition.